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0 °C

A solution of 2-(bromomethyl)propenoic acid t-butyl ester (20 g, 90.5 mmole) in dry acetonitrile (360 ml), cooled to 0° C., was treated with solid potassium carbonate (15.63 g, 113 mmole), followed by a solution of dibenzylamine (17.83 g, 90.5 mmole), in dry acetonitrile (600 ml), producing a 10° C. exotherm. The reaction was stirred at 0° C. for 0.5 hours, followed by 1 hour at room temperature, and then partitioned between water and diethyl ether. The ether phase was washed again with water, dried (sodium sulphate) and evaporated to yield the crude product (31 g) which was filtered through a pad of silica, eluting with hexane/CH2Cl2 (1:1), to yield 2-(dibenzylaminomethyl)propenoic acid t-butyl ester (23.8 g, 78%) as a solid, m.p. 62°-63° C. Found: C,78.09; H,8.20; N,4.18. C22H27NO2 requires C,78.3; N,8.06; N,4.15 %.

1. customproducing a 10° C. exotherm
2. waitfollowed by 1 hour at room temperature
3. custompartitioned between water and diethyl ether
4. washThe ether phase was washed again with water
5. dry with materialdried (sodium sulphate)
6. customevaporated
7. customto yield the crude product (31 g) which
8. filtrationwas filtered through a pad of silica
9. washeluting with hexane/CH2Cl2 (1:1)